


Flip Flop

by WriteReal



Category: Arrow (TV 2012)
Genre: 100 percent AU, AU, F/M
Language: English
Status: In-Progress
Published: 2019-04-09
Updated: 2019-04-09
Packaged: 2020-01-07 06:56:31
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,250
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18405455
Author URL: https://archiveofourown.org/users/WriteReal/pseuds/WriteReal
Summary: Oliver and Felicity attend the same prep school. At age fifteen, Oliver is looking for his first time, and Felicity has already been there with a former instructor. We are flip flopping the sexual experience canon, however, Felicity is not going to be a slut. The question is, will she take Oliver Queen's cherry? And whether or not that happens, is there a future for them?





	Flip Flop

**Author's Note:**

> At this rate this is rated Teen for conversations about sex. The rating may or may not change in the future. I just liked the idea of swapping their sexual experiences. Cooper is not a psycho in this one, and at this point, I don't think Oliver winds up on the island. That is subject to change based on what where the Muse leads me. Let me know if you like it. I'm at WriteReal1 on Twitter. Also, I have NOT abandoned by other fics! They will be continued!

Oliver licked his lips and checked the mirror again. His young face and blue eyes stared back at him. He scowled. Atalmost sixteen he still had a baby face. He ran his hand over his jaw. Peach fuzz. His dad had said he was 17 before he had grown real facial hair. That felt like forever.

He tugged down his t-shirt and admired the way it molded to his body. He had spent most of the spring and early summer in the gym. It wasn’t just to attract girls, and women – but that was definitely a big plus. He just liked the feeling of being strong. It made him feel older; more capable. It was also something that was just his. Oliver Queen, scion to a billionaire’s fortune, owed nothing and no one else to his increasingly chiseled physic. This was all him.

He turned away from the mirror and picked up his wallet and shoved it into his worn pocket. His blue Lamborghini was waiting down in the drive, newly detailed and shiny. He had picked that color because Laurel said it matched his eyes. He frowned again and pushed his thoughts away from his on-again-off again girlfriend. He was too young to have a steady girlfriend. He wanted to explore and learn. He wanted some experience and he knew that Laurel had none, and was not willing to go all the way yet. He actually hadn’t pushed that hard. It was conceited, but he didn’t want to deflower her when he didn’t know what the hell he was doing.

He had seen pornos of course, but young as he was he knew there was more to sex than that. The women in those videos were acting, faking their pleasure as much as their boobs and lips were fake. He didn’t want to fuck a porn star. They held no interest for him. He wanted a real girl; someone who could teach him what it really took to pleasure them.

He jogged down the stairs and smiled at Raissa who was walking through the foyer, no doubt on her way to the kitchen. He headed for the front door, eschewing a good-bye with his mother. His father was no doubt still at the office or out on a golf course somewhere. He had dutifully told his mother he was going out. She wouldn’t expect him back until midnight though he often came in well past that curfew.

As he walked out to circular drive and slid into the sleek sports car. He had a school permit to drive only to and from school, but he drove where and when he wanted. The police would stop him but, there would never be a ticket once they saw his name on the permit. 

His thoughts honed in on his date. For all his money, Felicity Smoak was out of his league. Not only was she by far the smartest in their private prep school, but she had already been accepted to MIT at the age of fifteen. She was taking early classes there this summer, and it was a given she would be graduating from their prep school early. She was leaving for Boston in a week, and that was part of what made her so desirable. Her long blonde hair, blue eyes, and toned body certainly didn’t hurt. They could have a good time, and then she would be gone, no strings attached. Well, that and the fact that he knew she had experience. It was well known that she and the robotics instructor, Cooper Seldon, had been having a relationship for the last year.

Oliver roared down the driveway, shifting easily, and slowing to press the remote for the huge iron gates. As soon as they parted enough to slip through, he gunned the huge engine, and the car leapt forward, roaring as his command and rocketing him towards his first true sexual encounter. 

 

Felicity touched up her lipstick and checked her blush again, making sure it wasn’t too dark. She and Oliver were going to the movies and then out to Big Belly Burger for a late dinner. What came after that had not been discussed, but she well knew what the sophomore wanted. Her affair with Cooper was well known. As far as the whole school knew, Oliver was still a virgin because he was with Laurel who, rumor had it, was holding out on him., It frankly surprised her that Oiver had waited. But he and Laurel were currently split and it looked like he wanted to be de-flowered before their inevitable reunited.

Felicity was experienced, she was leaving, and she was willing to go on a date with him despite the fact that it was well known that he and Laurel had been on and off for the last two years. Oliver expected to get lucky tonight, for the first time, and she was still undecided about whether or not that was going to happen.

Oliver was attractive, and he had spent the spring and first part of summer working out. He had shot up to over six feet as well. His blue eyes were gorgeous, but his refusal to treat anyone with anything other than a smirk or a come-on turned her off. She had been attracted to Cooper because he was smart and serious. Okay, and experienced. She had heard enough horror stories about first times with bumbling boys who thought the vagina was the main source of a woman’s pleasure or who only knew what sex was like from pornos. Nuh uh; she was not going to waste her time with any of that.

Cooper had been an enthusiastic and attentive lover. She knew he reveled in being her first. But, despite her iffy grasp of the English language when uncomfortable or flustered, she had made it clear enough that she wanted more that just wham-bam-thank-you-ma’am-I-got-your-cherry. He had been gentle but passionate, considerate but in charge. As a result, her first time had been minimum pain, maximum pleasure, and a newfound appreciation for why people were so focused on sex.

She rubbed a mixture of jasmine and vanilla essential oils on her pulse points and stepped back to assess herself. She looked young and fresh and…willing. Yes, she was going to drive Oliver Queen to the fracking brink tonight whether she decided to do the deed with him or not.

She turned from the mirror and strode over to scoop her clutch off the bed. She felt incredibly grown-up using her mom’s satin pink clutch. It was a bit over the top for a movie and burgers, but she felt it signaled her maturity. She was no ordinary 16-year old, and she had no problem displaying it. Of course, her mother had a bit of problem with it. She had had a real problem with Cooper.

Felicity had been surprised at how adamantly Donna had objected to the relationship with Cooper. Her mom dressed like she was 25 and dated a lot. She had long blonde hair, flawless make-up, and was well known in Starling City social circles as an excellent candidate for a trophy wife, even if she wasn’t the 25 she looked to be. The fact that Donna had no interest in being a trophy wife only added to her allure.

But Donna, knowing Felicity was so much more than a pretty face, had gotten right in Cooper’s face and told him that if he touched her daughter she would see him fired and charged with statutory rape. No matter how much Felicity had argued that her mother – who was 43 and currently dating a 32-year old -- was a hypocrite, Donna had refused to budge. So Felicity and Cooper had snuck around, and Donna had been blissfully ignorant. Occasionally, Felicity would date boys from school just to assuage her mother’s suspicions, but she had always made it clear to the boy at the end of the date that she was not interested. 

 

When Oliver rang the doorbell Felicity’s mother had literally bounced to the door, giving Oliver a bright smile as she opened the door. Donna had no intention of becoming a trophy wife and she certainly didn’t want that for her brilliant daughter, but she did want her girl to realize and feel how gorgeous and wonderful she was. So, if she wanted to go out with a boy who had the world at his feet, so be it. 

She pushed open the door and smiled widely at the rich, arrogant young man. If anyone could take him down a peg or two, it would Felicity. Money and looks did not turn Fel’s head, though Donna was bewildered as to what did. The boys her daughter had dated in the past seemed to have only one thing in common; they were vanilla, boring, and utterly forgettable.

Oliver, with his billions and confidence (okay, arrogance) did not fit the norm. So she eyed him suspiciously even as she welcomed into her home.

“She’ll be down in a minute,” she said sweetly. “Probably fixing her hair one last time.”

“That’s fine,” Oliver said with his well-practiced and generic smile. “She’s worth waiting for.”

Donna mentally rolled her eyes but smiled at the young man. She’d been a teenager not that long ago. This young stud in front of her had but one goal; to have sex with daughter. He wasn’t worthy, and she was going to remind Felicity of that.

Donna bade him to wait in the foyer while she ascended the stairs to check on Felicity’s status. She knew her daughter would keep the young scion waiting. What she wasn’t sure of was why. Oliver Queen was not Felicity’s usual date material. He was mediocre at school and a troublemaker. One fling before she leaves, Donna told herself. Before she goes off to MIT and gets a head start on an amazing, brilliant future. Donna didn’t have name or details, but she knew by the way Felicity carried herself around men that she was no longer a virgin. The knowledge at once made her cringe and eyet mbrace her almost-adult daughter’s sexuality, After all, Donna, raised in Vegas, and had lost her innocence far younger. 

“He’s here,” Donna sang as she sailed into Felicity’s room. Her daughter was a vision; she young, so flawless, It made Donna’s heart clench. “Fel, don’t have sex with him. He’s not worth it.”

Felicity smiled at her mother. In a rare moment of unbridled honesty she said, “I know. He’s a virgin, looking to get laid by someone who is leaving in a week so no strings attached.”

Donna gasped, her blue eyes wide at Felicity’s matter-of-a-fact interpretation of the cold, hard truth. 

“Okay. So don’t go there.”

“Hmm,” Felicity said, cocking her head to the side. “He’s just another guy, Mom. It's kind of a kick that the almighty Oliver Queen asked me out on a date.”

“Fel, hon,” Donna said, moving forward to grasp her daughter’s arms. “He’s nothing, baby girl. His parents are billionaires. They are the ones that built Queen Consolidated. He’s just the son that was born with a platinum spoon his mouth. He’s really nobody, Fel. Please keep that in mind.” 

Felicity impulsively pulled her mom into a hug. “Don’t worry, Mom. I know exactly who Oliver is, and I am not star struck. He’s a cocky rich boy, but he’s also really cute, and I’m going to enjoy his attention just for the helluva it.” She felt a twinge as she half lied to her mom. If she felt so moved, she was going to take Oliver’s cherry. If she did make that decision, she was going to make sure there were some very solid ground rules. Her hacking skills were neophyte compared to others, but she knew enough to make his life a living hell if he even thought about bragging about bedding her, and she would make it very clear to him that she would do just that.

Donna hugged her tight, and when she pulled back she had a full-on grin.

“How did you get so wise to men?”

Felicity laughed. “From you, Mom. You go out, you have fun. You have relationships with men who aren’t trying to make you arm candy or a trophy wife. You have never allowed yourself to be anything that a strong, confident, independent woman, and I want to be just like you.”

Tears filled Donna’s eyes. “Teaching you the wrong thing when it comes to men is one of my greatest fears. You don’t have a father figure. You don’t have a two-person family with a solid couple to model a healthy relationship for you. You—“

Felicity gave her mom a little shake. “You are the best model I could ever had. Dad left on his own. He’s stayed gone on his own. You stepped and showed me how to survive heart ache; how to move ahead. Uncle Dig and Aunt Lyla have shown me that a loving, strong relationship is possible. But when I grow up, I want to be like you.”

Tears slid down Donna’s face and she hugged her daughter tightly before pulling back. She sniffed. “Okay, you’ve kept him waiting long enough. Let him get an eyeful of that dress even if it is a bit too old for you.”

Felicity laughed and rolled her eyes, before picked up her mom’s clutch, kissing her on the cheek, and heading for the stairs.


End file.
